Organic compound, and electronic element and electronic device using same

ABSTRACT

The present disclosure relates to an organic compound. The structure of the organic compound consists of a structure represented by formula (I) and a structure represented by formula (II); the structure represented by formula (I) is fused with the structure represented by formula (II); and * represents a connection point, in formula (I), capable of being fused with formula (II). When being used to the organic light-emitting layer of an organic electroluminescent device, the organic compound of the present application can effectively improve the device efficiency of the device and prolong the service life of the organic electroluminescent device.

CROSS REFERENCE TO RELATED APPLICATIONS

The present application claims the priority of Chinese PatentApplication No. 202010695858.X, filed on Jul. 17, 2020, the contents ofwhich are incorporated herein by reference in their entirety as a partof the present application.

FIELD OF THE TECHNOLOGY

The present disclosure belongs to the technical field of organicmaterials, and in particular provides an organic compound, and anelectronic element and electronic device using the same.

BACKGROUND

Organic electroluminescent materials (OLEDs) have the advantages ofultra-thinness, self-luminescence, wide viewing angle, fast response,high luminous efficiency, good temperature adaptability, simpleproduction process, low driving voltage, low energy consumption, and thelike as a new-generation display technology, and have been widely usedin industries such as flat panel display, flexible display, solid statelighting, and vehicle display.

An organic light-emitting device generally includes an anode, a cathodeand an organic material layer between them. The organic material layeris typically formed in a multilayer structure composed of differentmaterials to improve the brightness, efficiency, and service life of anorganic electroluminescent device, and the organic material layer may becomposed of a hole injection layer, a hole transport layer, alight-emitting layer, an electron transport layer, an electron injectionlayer, and the like. In an organic light-emitting device structure, whena voltage is applied between two electrodes, holes and electrons areinjected into the organic material layer from the anode and the cathode,respectively, and excitons are formed when the injected holes andelectrons meet, and light is emitted when these excitons return to aground state.

In the existing organic electroluminescent device, the most majorproblem is the service life and efficiency, as the area of the displayincreases, the driving voltage is also increased, the luminousefficiency and the power efficiency are also required to be increased,and thus, it is necessary to continue to develop new materials tofurther improve the performance of the organic electroluminescentdevice.

SUMMARY

The present disclosure aims to provide an organic compound, and anelectronic element and electronic device using the same. The organiccompound can be used in an organic electroluminescent device, so thatthe performance of the device can be improved.

To achieve the above purpose, in a first aspect, the present disclosureprovides an organic compound, having a structure consisting of astructure represented by a formula I and a structure represented by aformula II:

where the structure represented by the formula I is fused with at leastone structure represented by the formula II;

* represents a site where the formula I is fused with the formula II;

a ring A is selected from a benzene ring or a fused aromatic ring with10 to 14 ring-forming carbon atoms;

n₁ represents the number of R₁, n₂ represents the number of R₂, and n₃represents the number of R₃;

R₁, R₂ and R₃ are represented by R_(k), n₁ to n₃ are represented byn_(k), and k is a variable and represents 1, 2 or 3; when k is 1, n_(k)is selected from 0, 1, 2, 3 or 4; when k is 2, n_(k) is selected from 0,1 or 2; when k is 3, n_(k) is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;and when n_(k) is greater than 1, any two n_(k) are the same ordifferent; and optionally, any two adjacent R_(k) are connected to eachother to form a ring, and the formed ring is optionally substituted withR′;

R₁, R₂, R₃, and R′ are the same or different, and are each independentlyselected from an alkyl with 1 to 5 carbon atoms or a structurerepresented by a formula III:

represents a chemical bond;

m represents the number of L, and m is selected from 1, 2 or 3; and whenm is 2 or 3, any two L are the same or different;

Ar is selected from a substituted or unsubstituted aryl with 6 to 30carbon atoms, a substituted or unsubstituted heteroaryl with 3 to 30carbon atoms, a triarylsilyl with 18 to 30 carbon atoms, atriarylphosphinyloxy with 12 to 20 carbon atoms, or a cycloalkyl with 3to 10 carbon atoms;

L is selected from a single bond, a substituted or unsubstituted arylenewith 6 to 30 carbon atoms, or a substituted or unsubstitutedheteroarylene with 3 to 30 carbon atoms;

substituents in L and Ar are one or more, where the substituents in Land Ar are each independently selected from deuterium, a halogen group,cyano, a heteroaryl with 3 to 12 carbon atoms, an aryl with 6 to 12carbon atoms, an alkyl with 1 to 5 carbon atoms, a cycloalkyl with 3 to10 carbon atoms, trimethylsilyl, or triphenylsilyl; and

X and Y are the same or different, and are each independently selectedfrom a single bond, O, S, C(R₄R₅), and Si(R₆R₇), and X and Y are notsimultaneously a single bond; where R₄-R₇ are the same or different, andare each independently selected from an alkyl with 1 to 5 carbon atoms,an aryl with 6 to 30 carbon atoms, or a heteroaryl with 2 to 30 carbonatoms; optionally, R₄ and R₅ are connected to each other to form a 3- to15-membered saturated or unsaturated ring together with the atoms towhich they are commonly connected; and optionally, R₆ and R₇ areconnected to each other to form a 3- to 15-membered saturated orunsaturated ring together with the atoms to which they are commonlyconnected.

In a second aspect, the present disclosure provides an electronicelement, including an anode and a cathode which are oppositely disposed,and a functional layer disposed between the anode and the cathode; andthe functional layer includes the organic compound provided by thepresent disclosure.

In a third aspect, the present disclosure provides an electronic device,including the electronic element according to the second aspect of thepresent disclosure.

The organic compound of the present disclosure has a large planarstructure formed by spiro[adamantane-fluorene] as a core structure fusedwith a benzoheteroaromatic ring; in this structure, an aromatic ring isfused on spiro[adamantane-fluorene], which greatly enhances the rigidityof the compound, improves the hole mobility, and possesses a high firsttriplet energy level, and the fused benzoheteroaromatic ring canefficiently promote energy transfer, and thus the organic compound canbe applied to a host material of an organic light-emitting layer in anorganic electroluminescent material; the compound can be applied to asingle-component host material or one of a two-component mixed-type hostmaterial, which can ensure that the organic electroluminescent devicehas high luminous efficiency and service life; and adamantane isspiro-bonded to the fused planar structure, which may effectively reduceintermolecular stacking, improve the film-forming properties of thecompound, and thus further improve the service life of the device.

Other features and advantages of the present disclosure will bedescribed in detail in the Detailed Description that follows.

BRIEF DESCRIPTION OF THE DRAWINGS

The accompanying drawings are used to provide a further understanding ofthe present disclosure, and constitute a part of this description, andtogether with the following specific examples, are used to explain thepresent disclosure, but do not constitute a limitation to the presentdisclosure.

FIG. 1 is a structural schematic diagram of an organicelectroluminescent device according to one example of the presentdisclosure.

FIG. 2 is a structural schematic diagram of an electronic deviceaccording to one example of the present disclosure.

DESCRIPTION OF REFERENCE SIGNS

100, anode; 200, cathode; 300, functional layer; 310, hole injectionlayer; 320, hole transport layer; 321, first hole transport layer; 322,second hole transport layer; 330, organic light-emitting layer; 340,electron transport layer; 350, electron injection layer; and 400,electronic device.

DETAILED DESCRIPTION

Specific examples of the present disclosure will be described in detailbelow. It should be understood that the specific examples described hereare only used to illustrate and explain the present disclosure, but arenot intended to limit the present disclosure.

In a first aspect, the present disclosure provides an organic compound,having a structure consisting of a structure represented by a formula Iand a structure represented by a formula II:

where the structure represented by the formula I is fused with at leastone structure represented by the formula II;

* represents a site where the formula I is fused with the formula II;

a ring A is selected from a benzene ring or a fused aromatic ring with10 to 14 ring-forming carbon atoms;

n₁ represents the number of R₁, n₂ represents the number of R₂, and n₃represents the number of R₃;

R₁, R₂ and R₃ are represented by R_(k), n₁ to n₃ are represented byn_(k), and k is a variable and represents 1, 2 or 3; when k is 1, n_(k)is selected from 0, 1, 2, 3 or 4; when k is 2, n_(k) is selected from 0,1 or 2; when k is 3, n_(k) is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;and when n_(k) is greater than 1, any two n_(k) are the same ordifferent; and optionally, any two adjacent R_(k) are connected to eachother to form a ring, and the formed ring is optionally substituted withR′;

R₁, R₂, R₃, and R′ are the same or different, and are each independentlyselected from an alkyl with 1 to 5 carbon atoms or a structurerepresented by a formula III:

represents a chemical bond;

m represents the number of L, and m is selected from 1, 2 or 3; and whenm is 2 or 3, any two L are the same or different;

Ar is selected from a substituted or unsubstituted aryl with 6 to 30carbon atoms, a substituted or unsubstituted heteroaryl with 3 to 30carbon atoms, a triarylsilyl with 18 to 30 carbon atoms, atriarylphosphinyloxy with 12 to 20 carbon atoms, or a cycloalkyl with 3to 10 carbon atoms;

L is selected from a single bond, a substituted or unsubstituted arylenewith 6 to 30 carbon atoms, or a substituted or unsubstitutedheteroarylene with 3 to 30 carbon atoms;

sub stituents in L and Ar are one or more (when L and Ar includesubstituents), and the substituents in L and Ar are each independentlyselected from deuterium, a halogen group, cyano, a heteroaryl with 3 to12 carbon atoms, an aryl with 6 to 12 carbon atoms, an alkyl with 1 to 5carbon atoms, a cycloalkyl with 3 to 10 carbon atoms, trimethylsilyl, ortriphenylsilyl; and

X and Y are the same or different, and are each independently selectedfrom a single bond, O, S, C(R₄R₅), and Si(R₆R₇), and X and Y are notsimultaneously a single bond; R₄ to R₇ are the same or different, andare each independently selected from an alkyl with 1 to 5 carbon atoms,an aryl with 6 to 30 carbon atoms, or a heteroaryl with 2 to 30 carbonatoms; optionally, R₄ and R₅ are connected to each other to form a 3- to15-membered saturated or unsaturated ring together with the atoms towhich they are commonly connected; and optionally, R₆ and R₇ areconnected to each other to form a 3- to 15-membered saturated orunsaturated ring together with the atoms to which they are commonlyconnected.

In the present disclosure, R₁, R₂, R₃, and R′ may also eachindependently be selected from deuterium, a halogen group, and cyano.

In the present disclosure “* represents a site where the formula I isfused with the formula II”, which means that the formula II is connectedto any two adjacent fused positions of eight fused sites of the formulaI.

Optionally, the structure represented by the formula I is fused with onestructure represented by the formula II.

Optionally, the structure represented by the formula I is fused with twostructures represented by the formula II.

Optionally, the structure represented by the formula I is fused withthree structures represented by the formula II.

In the present disclosure, “

” means that m L are linked together in sequence, and are linked to Ar,specifically, when m is 1,

represents

when m is 2,

represents

; when m is 3,

represents

and when m is 2 or 3, each L may be the same or different.

In the present disclosure, the terms “optional” and “optionally” meanthat the subsequently described event or circumstance can but need notoccur, and that the description includes occasions where the event orcircumstance occurs or does not occur. For example, “optionally, twoadjacent substituents xx form a ring”, which means that the twosubstituents can, but need not, form a ring, including a scenario inwhich two adjacent substituents form a ring and a scenario in which twoadjacent substituents do not form a ring. For another example,“optionally, R₄ and R₅ are connected to each other to form a 3- to15-membered saturated or unsaturated ring together with the atoms towhich they are commonly connected”, which means that R₄ and R₅ may beconnected to each other to form a 3- to 15-membered saturated orunsaturated ring together with the atoms to which they are commonlyconnected, or R₄ and R₅ may also each independently be present.

In the present disclosure, if a group is not specifically indicated tobe substituted, it indicates that the group is unsubstituted.

In the present disclosure, the used descriptions modes “each . . . isindependently”, “ . . . is respectively and independently” and “ . . .is independently selected from” can be interchanged, which should beunderstood in a broad sense, and may mean that specific optionsexpressed by a same symbol in different groups do not influence eachother, or may also mean that specific options expressed by a same symbolin a same group do not influence each other. For example, the meaning of“

where each q is independently 0, 1, 2 or 3 and each R″ is independentlyselected from hydrogen, deuterium, fluorine, and chlorine” is asfollows: a formula Q-1 represents that a benzene ring has q substituentsR″, each R″ can be the same or different, and options of each R″ do notinfluence each other; and a formula Q-2 represents that each benzenering of biphenyl has q substituents R″, the number q of the substituents R″ on the two benzene rings can be the same or different, eachR″ can be the same or different, and options of each R″ do not influenceeach other.

In the present disclosure, the term “substituted or unsubstituted” meansthat a functional group described behind the term may or may not havesubstituents (the substituents are collectively referred to as Rc belowfor ease of description). For example, “substituted or unsubstitutedaryl” refers to aryl with a substituent Rc or unsubstituted aryl. Theabove substituent, i.e. Rc, can be, for example, deuterium, a halogengroup, cyano, heteroaryl, aryl, trimethylsilyl, triphenylsilyl, alkyl orcycloalkyl.

In the present disclosure, in the expression that “any two adjacentsubstituents form a ring”, “any adjacent” can include the condition thatthere are two substituents on a same atom and can also include thecondition that two adjacent atoms each have one substituent; when thereare two sub stituents on the same atom, the two sub stituents may form asaturated or unsaturated ring (e.g., a 3- to 18-membered saturated orunsaturated ring) with the atom to which they are commonly connected;when two adjacent atoms each have one substituent, the two substituentsmay be fused to form a ring, e.g., a naphthalene ring, a phenanthrenering, or an anthracene ring. For example, “any two adjacent R₁ form aring”, which includes the condition that any two adjacent R₁ areconnected to each other to form a ring with the atoms to which they arecommonly connected, or the condition that any two adjacent R₂ areconnected to each other to form a ring with the atoms to which they arecommonly connected, or the condition that any two adjacent R₃ areconnected to each other to form a ring with the atoms to which they arecommonly connected. For example: any two adjacent R₁ may form a ringhaving 6 to 15 carbon atoms, or a ring having 6 to 10 carbon atoms; thering may be saturated (e.g., a five-membered ring

a six-membered ring

etc.) or unsaturated, (for example, an aromatic ring, and specificexamples of the aromatic ring include a benzene ring

a naphthalene ring

a phenanthrene ring

etc.).

In the present disclosure, the number of carbon atoms of a substitutedor unsubstituted functional group refers to the number of all carbonatoms. For example, if Ar is a substituted aryl with 12 carbon atoms,then the number of all carbon atoms of the aryl and substituents on thearyl is 12.

In the present disclosure, aryl refers to an optional functional groupor substituent derived from an aromatic carbocyclic ring. The aryl canbe monocyclic aryl (e.g., phenyl) or polycyclic aryl, in other words,the aryl can be monocyclic aryl, fused aryl, two or more monocyclic arylconjugatedly linked by carbon-carbon bonds, monocyclic aryl and fusedaryl which are conjugatedly linked by a carbon-carbon bond, and two ormore fused aryl conjugatedly linked by carbon-carbon bonds. That is,unless specified otherwise, two or more aromatic groups conjugatedlylinked by carbon-carbon bonds can also be regarded as aryl of thepresent disclosure. The fused aryl may, for example, include bicyclicfused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthryl,fluorenyl, and anthryl), and the like. The aryl does not containheteroatoms such as B, N, O, S, P, Se, and Si. For example, in thepresent disclosure, biphenyl, terphenyl, and the like are aryl. Examplesof the aryl can include, but are not limited to, phenyl, naphthyl,fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, quaterphenyl,quinquephenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthenyl,chrysenyl, and the like. In the present disclosure, involved arylenerefers to a divalent group formed by further loss of one hydrogen atomof the aryl.

In the present disclosure, substituted aryl can be that one or two ormore hydrogen atoms in the aryl are substituted with groups such as adeuterium atom, a halogen group, —CN, aryl, heteroaryl, trialkylsilyl,alkyl, cycloalkyl, and the like. Specific examples ofheteroaryl-substituted aryl include, but are not limited to,dibenzofuranyl-substituted phenyl, dibenzothiophenyl-substituted phenyl,pyridinyl-substituted phenyl, and the like. It should be understood thatthe number of carbon atoms of the substituted aryl refers to the totalnumber of carbon atoms of the aryl and substituents on the aryl, forexample, substituted aryl with 18 carbon atoms means that the totalnumber of carbon atoms of the aryl and substituents is 18.

In the present disclosure, examples of aryl as a substituent include,but are not limited to, phenyl, biphenyl, naphthyl,9,9-dimethylfluorenyl, anthryl, phenanthryl, and chrysenyl.

In the present disclosure, heteroaryl refers to a monovalent aromaticring containing at least one heteroatom in the ring or its derivative,and the heteroatom can be at least one of B, O, N, P, Si, Se, and S. Theheteroaryl may be monocyclic heteroaryl or polycyclic heteroaryl, inother words, the heteroaryl may be a single aromatic ring system or aplurality of aromatic ring systems conjugatedly connected viacarbon-carbon bonds, and any one aromatic ring system is one aromaticmonocyclic ring or one aromatic fused ring. For example, the heteroarylmay include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl,oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl,acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl,phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl,pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl,benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl,dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl,isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl,dibenzofuranyl, as well as N-phenylcarbazolyl, N-pyridylcarbazolyl,N-methylcarbazolyl and the like, but is not limited to this. Thienyl,furyl, phenanthrolinyl, etc. are heteroaryl of the single aromatic ringsystem, and N-arylcarbazolyl, and N-heteroarylcarbazolyl are heteroarylof the plurality of aromatic ring systems conjugatedly connected viacarbon-carbon bonds. In the present disclosure, involved heteroarylenerefers to a divalent group formed by further loss of one hydrogen atomof the heteroaryl.

In the present disclosure, substituted heteroaryl can be that one or twoor more hydrogen atoms in the heteroaryl are substituted with groupssuch as a deuterium atom, a halogen group, —CN, aryl, heteroaryl,trialkylsilyl, alkyl, cycloalkyl, and the like. Specific examples ofaryl-substituted heteroaryl include, but are not limited to,phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl,phenyl-substituted pyridyl, and the like. It should be understood thatthe number of carbon atoms of the substituted heteroaryl refers to thetotal number of carbon atoms of the heteroaryl and substituents on theheteroaryl.

In the present disclosure, heteroaryl as a substituent includes, forexample, but is not limited to, pyridyl, pyrimidinyl, carbazolyl,dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl,and isoquinolyl.

In the present disclosure, an unpositioned connecting bond refers to asingle bond “

” extending from a ring system, which indicates that one end of theconnecting bond can be connected to any position in the ring systemthrough which the bond penetrates, and the other end of the connectingbond is connected to the remaining part of a compound molecule.

For example, as shown in a formula (f) below, naphthyl represented bythe formula (f) is connected to other positions of a molecule by twounpositioned connecting bonds penetrating a bicyclic ring, and itsmeaning includes any one possible connection mode represented byformulae (f-1) to (f-10).

For another example, as shown in a formula (X′) below, phenanthrylrepresented by the formula (X′) is connected to other positions of amolecule via one unpositioned connecting bond extending from the middleof a benzene ring on one side, and its meaning includes any one possibleconnection mode represented by formulae (X′-1) to (X′-4).

An unpositioned substituent in the present disclosure refers to asubstituent connected through a single bond extending from the center ofa ring system, which means that the substituent can be connected to anypossible position in the ring system. For example, as shown in a formula(Y) below, a substituent R′ as shown in the formula (Y) is connected toa quinoline ring via one unpositioned connecting bond, and its meaningincludes any one possible connection mode represented by formulae (Y-1)to (Y-7).

In the present disclosure, the number of carbon atoms of alkyl may be 1to 5, and the alkyl may include linear alkyl with 1 to 5 carbon atomsand branched alkyl with 3 to 5 carbon atoms. The number of carbon atomsmay be any integer of 1, 2, 3, 4, or 5; and specific examples of thealkyl can include, methyl, ethyl, n-propyl, isopropyl, n-butyl,isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and the like.

In the present disclosure, the number of carbon atoms of cycloalkyl canbe, for example, 3, 5, 6, 7, 8, 9 or 10. Specific examples of thecycloalkyl include, but are not limited to, cyclopentyl, cyclohexyl, andadamantyl.

In the present disclosure, the halogen group can be, for example,fluorine, chlorine, bromine or iodine.

In the present disclosure, specific examples of trialkylsilyl include,but are not limited to, trimethylsilyl, triethylsilyl, and the like.

In the present disclosure, specific examples of triarylsilyl include,but are not limited to, triphenylsilyl and the like.

In the present disclosure, in the above two groups of groups R₄ and R₅,as well as R₆ and R₇, two groups in each group are connected to eachother to form a 3- to 15-membered saturated or unsaturated ring togetherwith the atoms to which they are commonly connected. For example, in theformula II

when Y is a single bond, n₃ is 0, and X is C(R₄R₅), and when R₄ and R₅are connected to each other to form a 5-membered ring together with theatoms to which they are commonly connected, the formula II is

likewise, the formula II may also represent

that is, R₄ and R₅ are connected to each other to form a 6-membered ringtogether with the atoms to which they are commonly connected; likewise,the formula II may also represent

that is, R₄ and R₅ are connected to each other to form a partiallyunsaturated 13-membered ring together with the atoms to which they arecommonly connected; and likewise, the formula II may also represent

that is, R₄ and R₅ are connected to each other to form a 10-memberedring together with the atoms to which they are commonly connected.

In one example of the present disclosure, the organic compound has astructure shown in any one of formulae 1-1 to 1-17:

where n′₁ is selected from 0, 1 or 2; and n′₂ is selected from 0, 1 or2. X and Y may be the same or different.

In one example of the present disclosure, the organic compound has astructure shown in any one of 2-1 to 2-41:

where n′₂ is selected from 0, 1 or 2.

In one example of the present disclosure, the formula II has a structureshown in any one of formulae II-1 to II-11:

Optionally, n₁, n₂, and n₃ are not simultaneously 0, and at least oneR_(k), if present, has the structure represented by the formula III. Forexample, n₁=1, and R₁ has the structure represented by the formula III;or n₂=1, and R₂ has the structure represented by the formula III; orn₃=1, and R₃ has the structure represented by the formula III.

In the present disclosure, a ring A refers to

where the ring A is a benzene ring or a fused aromatic ring with 10 to14 ring-forming carbon atoms. The fused aromatic ring may be, forexample, a naphthalene ring, an anthracene ring, or a phenanthrene ring.Where

represents a chemical bond. For example, in a compound

the ring A is a benzene ring, the number of a substituent R₃ on the ringA is 0 (i.e., n₃=0), X represents C(R₄R₅), R₄ and R₅ are each methyl, Yis a single bond, and the number of a substituent R₁ and the number of asubstituent R₂ are also 0 (i.e., n₁ and n₂ are both 0).

In one example of the present disclosure, n₁, n₂ and n₃ may eachindependently be selected from 0, 1 or 2.

In the present disclosure, when R₁, R₂, and R₃ respectively have thestructure represented by the formula III, Ar in R₁, R₂, and R₃ may eachbe the same or different, and L may each also be the same or different.

In some examples, L is selected from a single bond or the groupconsisting of groups represented by formulae j-1 to j-15:

where M₂ is selected from a single bond or

and

represents a chemical bond;

Q₁ to Q₅ and Q′₁ to Q′₄ are each independently selected from N, C orC(J₁), and at least one of Q₁ to Q₅ is selected from N; when two or moreof Q₁ to Q₅ are selected from C(J₁), any two J₁ are the same ordifferent; and when two or more of Q′₁ to Q′₄ are selected from C(J₁),any two J₁ are the same or different;

Q₆ to Q₁₃ are each independently selected from N, C or C(J₂), and atleast one of Q₆ to Q₁₃ is selected from N; and when two or more of Q₆ toQ₁₃ are selected from C(J₂), any two J₂ are the same or different;

Q₁₄ to Q₂₃ are each independently selected from N, C or C(J₃), and atleast one of Q₁₄ to Q₂₃ is selected from N; and when two or more of Q₁₄to Q₂₃ are selected from C(J₃), any two J₃ are the same or different;

Q₂₄ to Q₂₅ are each independently selected from N, C or C(J₄);

Q₂₆ and Q₂₇ are each independently selected from N, C or C(J₅), and atleast one of Q₂₆ to Q₂₇ is selected from N; and when Q₂₆ and Q₂₇ areboth selected from C(J₅), both J₅ are the same or different;

E₁ to E₁₄, and J₁ to J₅ are each independently selected from hydrogen,deuterium, fluorine, chlorine, bromine, cyano, a heteroaryl with 3 to 10carbon atoms, an aryl with 6 to 12 carbon atoms, trimethylsilyl,triphenylsilyl, an alkyl with 1 to 5 carbon atoms, or a cycloalkyl with3 to 10 carbon atoms;

e₁ to e₁₄ are represented by e_(r), E₁ to E₁₄ are represented by E_(r),r is a variable, and represents any integer from 1 to 14, and e_(r)represents the number of a sub stituent E_(r); when r is selected from1, 2, 3, 4, 5, 6, 9, 13 or 14, e_(r) is selected from 1, 2, 3 or 4; whenr is selected from 7 or 11, e_(r) is selected from 1, 2, 3, 4, 5 or 6;when r is 12, e_(r) is selected from 1, 2, 3, 4, 5, 6, or 7; when r isselected from 8 or 10, e_(r) is selected from 1, 2, 3, 4, 5, 6, 7 or 8;and when e_(r) is greater than 1, any two E_(r) are the same ordifferent, and optionally, any two adjacent E_(r) are connected to eachother to form a ring;

K₁ is selected from O, S, Se, N(E₁₅), C(E₁₆E₁₇) or Si(E₁₈E₁₉); whereE₁₅, E₁₆, E₁₇, E₁₈ and E₁₉ are each independently selected from an arylwith 6 to 20 carbon atoms, a heteroaryl with 3 to 20 carbon atoms, analkyl with 1 to 5 carbon atoms, or a cycloalkyl with 3 to 10 carbonatoms, or E₁₆ and E₁₇ are connected to each other to form a saturated orunsaturated ring having 3 to 15 carbon atoms together with the atoms towhich they are commonly connected, or E₁₈ and E₁₉ are connected to eachother to form a saturated or unsaturated ring having 3 to 15 carbonatoms together with the atoms to which they are commonly connected; and

K₂ is selected from a single bond, O, S, Se, N(E₂₀), C(E₂₁E₂₂) orSi(E₂₃E₂₄); where E₂₀ to E₂₄ are each independently selected from anaryl with 6 to 20 carbon atoms, a heteroaryl with 3 to 20 carbon atoms,an alkyl with 1 to 5 carbon atoms, or a cycloalkyl with 3 to 10 carbonatoms, or E₂₁ and E₂₂ are connected to each other to form a saturated orunsaturated ring having 3 to 15 carbon atoms together with the atoms towhich they are commonly connected, or E₂₃ and E₂₄ are connected to eachother to form a saturated or unsaturated ring having 3 to 15 carbonatoms together with the atoms to which they are commonly connected.

In the present disclosure, in the four groups of groups E₁₆ and E₁₇, E₁₈and E₁₉, E₂₁ and E₂₂, as well as E₂₃ and E₂₄, a ring formed byconnecting two groups in each group to each other can be a saturated orunsaturated ring having 3 to 15 carbon atoms. For example, in theformula j-8

when both K₄ and M₁ are a single bond, Q′₁, Q′₂, Q′₃, Q′₄, and E₁₁ arehydrogen, and K₁ is C(E₁₆E₁₇), and when E₁₆ and E₁₇ are connected toeach other to form a 5-membered ring together with the atoms to whichthey are commonly connected, the formula j-8 is

likewise, the formula j-8 may also represent

that is, E₁₆ and E₁₇ are connected to each other to form a partiallyunsaturated 13-membered ring together with the atoms to which they arecommonly connected.

In the present disclosure, in the formulae j-10 to j-12, J₁ to J₃ may berepresented by J_(j), where j is a variable and represents 1, 2, or 3.For example, when j is 2, J_(j) refers to J₂. It should be understoodthat J_(j) in C(J_(j)) is not present when an unpositioned connectingbond is connected to C(J_(j)). For example, in the chemical formulai-11, when “

” is connected to Q₁₂, Q₁₂ can only represent a C atom, i.e. thestructure of the formula i-11 is specifically:

Optionally, L is selected from a single bond, substituted orunsubstituted arylene with 6 to 25 carbon atoms, and substituted orunsubstituted heteroarylene with 3 to 25 carbon atoms. For example, Lcan be selected from a single bond, substituted or unsubstituted arylenewith 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23,24, or 25 carbon atoms, and substituted or unsubstituted heteroarylenewith 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20,21, 22, 23, 24, or 25 carbon atoms.

Optionally, L is selected from a single bond, a substituted orunsubstituted arylene with 6 to 15 carbon atoms, or a substituted orunsubstituted heteroarylene with 3 to 20 carbon atoms.

Optionally, L is selected from a single bond or a substituted orunsubstituted group T₁, and the unsubstituted group T₁ is selected fromthe group consisting of:

the substituted group T₁ has one or two or more substituents, and thesubstituents in substituted group T₁ are independently selected fromdeuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, methyl,ethyl, isopropyl, tert-butyl, phenyl, biphenyl, pyridyl, naphthyl,carbazolyl, dibenzofuranyl or dibenzothienyl.

Further optionally, L is selected from a single bond or the groupconsisting of:

Optionally, L is selected from a single bond, or substituted orunsubstituted phenylene, substituted or unsubstituted naphthylene,substituted or unsubstituted anthrylene, substituted or unsubstituteddibenzofuranylene, substituted or unsubstituted dibenzothienylene,substituted or unsubstituted benzothiazolylene, substituted orunsubstituted benzoxazolylene, substituted or unsubstituted biphenylene,substituted or unsubstituted quinolylene, substituted or unsubstitutedquinazolinylene, substituted or unsubstituted benzo[f]quinoxalinylene,substituted or unsubstituted benzo[f]quinazolinylene, substituted orunsubstituted benzo[h]quinazolinylene, substituted or unsubstitutedfluorenylene, substituted or unsubstituted benzimidazolylene,substituted or unsubstituted phenanthro[9,10-d]imidazolylene,substituted or unsubstituted pyridylene, substituted or unsubstitutedcarbazolylene, substituted or unsubstituted triazinylene, substituted orunsubstituted quinoxalinylene, substituted or unsubstitutedphenanthrylene, substituted or unsubstituted pyrimidylene, substitutedor unsubstituted benzothienopyrimidinylene, substituted or unsubstitutedbenzofuropyrimidinylene, and substituted or unsubstituteddibenzo[f,h]quinoxalinylene; or is a group formed by connecting two orthree of the above groups by a single bond; and substituents in theabove groups are the same or different, and are each independentlyselected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl,tert-butyl, phenyl, phenyl substituted with methyl, ethyl, isopropyl,and tert-butyl, naphthyl, dimethylfluorenyl, biphenyl, biphenylsubstituted with phenyl, dibenzofuranyl, dibenzothienyl, carbazolyl,quinolyl, and pyridyl.

In some examples, Ar is selected from the group consisting of groupsrepresented by any one of formulae i-1 to i-15:

where M₁ is selected from a single bond or

G₁ to G₅ and G′₁ to G′₄ are each independently selected from N, C, orC(J₆), and at least one of G₁ to G₅ is selected from N; when two or moreof G₁ to G₅ are selected from C(J₆), any two J₆ are the same ordifferent; and when two or more of G′₁ to G′₄ are selected from C(J₆),any two J₆ are the same or different;

G₆ to G₁₃ are each independently selected from N, C or C(J₇), and atleast one of G₆ to G₁₃ is selected from N; and when two or more of G₆ toG₁₃ are selected from C(J₇), any two J₇ are the same or different;

G₁₄ to G₂₃ are each independently selected from N, C or C(J₈), and atleast one of G₁₄ to G₂₃ is selected from N; and when two or more of G₁₄to G₂₃ are selected from C(J₈), any two J₈ are the same or different;

G₂₄ is selected from O, S, N(J₉) or C(J₁₀);

Z₁ is selected from hydrogen, deuterium, a halogen group, cyano,trimethylsilyl, an alkyl with 1 to 5 carbon atoms, a cycloalkyl with 3to 10 carbon atoms, or triphenylsilyl;

Z₂ to Z₉, and Z₂₂ are each independently selected from hydrogen,deuterium, a halogen group, cyano, trimethylsilyl, an alkyl with 1 to 5carbon atoms, a cycloalkyl with 3 to 10 carbon atoms, a heteroaryl with3 to 18 carbon atoms, or triphenylsilyl;

Z₁₀ to Z₂₁, and J₁ to J₁₀ are each independently selected from hydrogen,deuterium, a halogen group, cyano, trimethylsilyl, an alkyl with 1 to 5carbon atoms, a cycloalkyl with 3 to 10 carbon atoms, an aryl with 6 to18 carbon atoms, a heteroaryl with 3 to 18 carbon atoms, ortriphenylsilyl;

h₁ to h₂₂ are represented by h_(k), Z₁ to Z₂₂ are represented by Z_(k),k is a variable and represents any integer from 1 to 22, and h_(k)represents the number of a substituent Z_(k); when k is selected from 5or 17, h_(k) is selected from 1, 2 or 3; when k is selected from 2, 7,8, 12, 15, 16, 18, 21 or 22, h_(k) is selected from 1, 2, 3 or 4; when kis selected from 1, 3, 4, 6, 9 or 14, h_(k) is selected from 1, 2, 3, 4or 5; when k is 13, h_(k) is selected from 1, 2, 3, 4, 5, or 6; when kis selected from 10 or 19, h_(k) is selected from 1, 2, 3, 4, 5, 6 or 7;when k is 20, h_(k) is selected from 1, 2, 3, 4, 5, 6, 7, or 8; when kis 11, h_(k) is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; and whenh_(k) is greater than 1, any two Z_(k) are the same or different;

K₁ is selected from O, S, N(Z₂₃), C(Z₂₄Z₂₅), and Si(Z₂₆Z₂₇); where Z₂₃,Z₂₄, Z₂₅, Z₂₆, and Z₂₇ are each independently selected from an aryl with6 to 18 carbon atoms, a heteroaryl with 3 to 18 carbon atoms, an alkylwith 1 to 5 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms, orZ₂₄ and Z₂₅ are connected to each other to form a saturated orunsaturated ring having 3 to 15 carbon atoms together with the atoms towhich they are commonly connected, or Z₂₆ and Z₂₇ are connected to eachother to form a saturated or unsaturated ring having 3 to 15 carbonatoms together with the atoms to which they are commonly connected; and

K₂ is selected from a single bond, O, S, N(Z₂₈), C(Z₂₉Z₃₀), andSi(Z₃₁Z₃₂); where Z₂₈, Z₂₉, Z₃₀, Z₃₁, and Z₃₂ are each independentlyselected from an aryl with 6 to 18 carbon atoms, a heteroaryl with 3 to18 carbon atoms, an alkyl with 1 to 5 carbon atoms, or cycloalkyl with 3to 10 carbon atoms, or Z₂₉ and Z₃₀ are connected to each other to form asaturated or unsaturated ring having 3 to 15 carbon atoms together withthe atoms to which they are commonly connected, or Z₃₁ and Z₃₂ areconnected to each other to form a saturated or unsaturated ring having 3to 15 carbon atoms together with the atoms to which they are commonlyconnected.

Optionally, Ar is selected from a substituted or unsubstituted aryl with6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl with 3to 20 carbon atoms. For example, Ar may be selected from substituted orunsubstituted aryl with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18,19, 20, 21, 22, 23, 24, or 25 carbon atoms, and substituted orunsubstituted heteroaryl with 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14,15, 16, 17, 18, 19, or 20 carbon atoms.

Optionally, Ar is selected from a substituted or unsubstituted group T₂,and the unsubstituted group T₂ is selected from the group consisting of:

the substituted group T₂ has one or two or more substituents, and thesubstituents in the substituted group T₂ are independently selected fromdeuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl,phenyl, biphenyl, pyridyl, naphthyl, carbazolyl, cyclohexyl,dibenzofuranyl or dibenzothienyl.

Further optionally, Ar is selected from the group consisting of:

In one example, Ar is selected from substituted or unsubstituted phenyl,substituted or unsubstituted pyridyl, substituted or unsubstitutedpyrimidinyl, substituted or unsubstituted triazinyl, substituted orunsubstituted naphthyl, substituted or unsubstituted anthryl,substituted or unsubstituted benzothiazolyl, substituted orunsubstituted benzoxazolyl, substituted or unsubstituted phenanthryl,substituted or unsubstituted biphenyl, substituted or unsubstitutedquinolyl, substituted or unsubstituted 1,10-phenanthrolinyl, substitutedor unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituteddibenzofuranyl, substituted or unsubstituted dibenzothienyl, substitutedor unsubstituted 9,10-benzophenanthryl, substituted or unsubstitutedN-phenylcarbazolyl, substituted or unsubstituted terphenyl, substitutedor unsubstituted carbazolyl, substituted or unsubstituted pyrenyl,substituted or unsubstituted fluoranthenyl, 1-phenyl-1H-benzimidazolyl,substituted or unsubstituted 9,9-spirobifluorenyl, substituted orunsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted4,5-diaza-9,9′-spirodifluorenyl, substituted or unsubstitutedsilafluorenyl, and substituted or unsubstituted benzofuropyrimidinyl,and substituents in the above groups are the same or different, and areeach independently selected from deuterium, cyano, fluorine,trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl,pyridyl, carbazolyl, and naphthyl.

Optionally, R₄ to R₇ are each independently selected from an alkyl with1 to 5 carbon atoms, an aryl with 6 to 20 carbon atoms, or a heteroarylwith 3 to 20 carbon atoms.

Further optionally, R₄ to R₇ are each independently selected frommethyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl,pyridyl, and quinolyl.

Optionally, the organic compound is selected from the group consistingof the following compounds:

A synthetic method of the organic compound provided is not particularlylimited in the present disclosure, and those skilled in the art candetermine a suitable synthetic method according to the organic compoundof the present disclosure in combination with synthetic methods providedin Synthesis examples. In other words, the Synthesis examples of thepresent disclosure exemplarily provide methods for the preparation ofthe organic compounds, and the used raw materials may be commerciallyobtained or obtained by a method well known in the art. All organiccompounds provided by the present disclosure can be obtained accordingto these exemplary synthetic methods by those skilled in the art, andall specific synthetic methods for preparing such organic compounds arenot described in detail here, which should not be understood by thoseskilled in the art as limiting the present disclosure.

In a second aspect, the present disclosure provides an electronicelement, including an anode and a cathode which are oppositely disposed,and a functional layer disposed between the anode and the cathode; andthe functional layer includes the organic compound described above.

The organic compound provided by the present disclosure can be used toform at least one organic film layer in the functional layer to improvethe efficiency and service life characteristics of the electronicelement.

In one example of the present disclosure, the functional layer includesan organic light-emitting layer including the organic compound. Theorganic light-emitting layer may be composed of the organic compoundprovided by the present disclosure or may be composed of the organiccompound provided by the present disclosure together with othermaterials.

Optionally, the electronic element is an organic electroluminescentdevice.

According to one example of the present disclosure, the organicelectroluminescent device can be a green device or a red device. Asshown in FIG. 1 , the organic electroluminescent device may include ananode 100, a first hole transport layer 321, a second hole transportlayer 322, an organic light-emitting layer 330 as an energy conversionlayer, an electron transport layer 340, and a cathode 200 which aresequentially stacked.

Optionally, the anode 100 includes the following anode materials, whichare preferably materials having a large work function that facilitatehole injection into the functional layer. Specific examples of the anodematerials include metals such as nickel, platinum, vanadium, chromium,copper, zinc, and gold or their alloys; metal oxides such as zinc oxide,indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO);combined metals and oxides such as ZnO:Al or SnO₂:Sb; or conductingpolymers such as poly(3-methylthiophene),poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, andpolyaniline, but are not limited to this. A transparent electrodecontaining indium tin oxide (ITO) as the anode is preferably included.

Optionally, the hole transport layer 320 includes a first hole transportlayer 321 and a second hole transport layer 322 which are sequentiallystacked, and the first hole transport layer 321 is closer to the anode100 than the second hole transport layer 322.

Optionally, the first hole transport layer 321 and the second holetransport layer 322 each include one or more hole transport materials,and the hole transport materials may be selected from a carbazolepolymer, carbazole-linked triarylamine compounds, or other types ofcompounds, which are not particularly limited in the present disclosure.For example, the first hole transport layer 321 may be composed of acompound NPB, HT-01 or HT-03; and the second hole transport layer 322may be composed of a compound HT-02 or HT-04. The structures of HT-01 toHT-04 are shown below.

Optionally, the organic light-emitting layer 330 may be composed of asingle light-emitting material, and may also include a host material anda guest material. The host material and/or the guest material of theorganic light-emitting layer may contain the organic compound of thepresent disclosure. Further optionally, the organic light-emitting layer330 is composed of the host material and the guest material, and holesinjected into the organic light-emitting layer 330 and electronsinjected into the organic light-emitting layer 330 may be recombined inthe organic light-emitting layer 330 to form excitons, the excitonstransfer energy to the host material, and the host material transfersenergy to the guest material, thus enabling the guest material to emitlight. In one example of the present disclosure, the host material ofthe organic light-emitting layer contains the organic compound of thepresent disclosure.

The guest material of the organic light-emitting layer 330 may be acompound having a condensed aryl ring or its derivative, a compoundhaving a heteroaryl ring or its derivative, an aromatic aminederivative, or other materials, which is not specially limited in thepresent disclosure.

The electron transport layer 340 may be of a single-layer structure or amulti-layer structure, and may include one or more electron transportmaterials, and the electron transport materials may be selected from,but are not limited to, a benzimidazole derivative, an oxadiazolederivative, a quinoxaline derivative, or other electron transportmaterials. In one example of the present disclosure, the electrontransport layer 340 may be composed of TPBi and LiQ or ET-01 (with astructure shown below) and LiQ.

In the present disclosure, the cathode 200 may include a cathodematerial, which is a material having a small work function thatfacilitates electron injection into the functional layer. Specificexamples of the cathode material include, but are not limited to, metalssuch as magnesium, calcium, sodium, potassium, titanium, indium,yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or theiralloys; or multilayer materials such as LiF/Al, Liq/Al, LiO₂/Al, LiF/Ca,LiF/Al, and BaF₂/Ca. A metal electrode containing magnesium and silveras the cathode is preferably included.

Optionally, as shown in FIG. 1 , a hole injection layer 310 may also bearranged between the anode 100 and the first hole transport layer 321 toenhance the ability to inject holes into the first hole transport layer321. The hole injection layer 310 can be made of a benzidine derivative,a starburst arylamine compound, a phthalocyanine derivative or othermaterials, which is not specially limited in the present disclosure. Forexample, the hole injection layer 310 may be composed of HAT-CN orF4-TCNQ.

Optionally, as shown in FIG. 1 , an electron injection layer 350 mayalso be arranged between the cathode 200 and the electron transportlayer 340 to enhance the ability to inject electrons into the electrontransport layer 340. The electron injection layer 350 may include aninorganic material such as an alkali metal sulfide and an alkali metalhalide, or may include a complex of an alkali metal and an organicsubstance. For example, the electron injection layer 350 may include LiQor Yb.

In a third aspect, the present disclosure provides an electronic device,including the electronic element according to the second aspect of thepresent disclosure.

According to one example, as shown in FIG. 2 , the electronic device isan electronic device 400 including the organic electroluminescent devicedescribed above. The electronic device 400 may be, for example, adisplay device, a lighting device, an optical communication device, orother types of electronic devices, and may include, for example, but isnot limited to, a computer screen, a mobile phone screen, a television,electronic paper, an emergency lighting lamp, an optical module, and thelike.

Compounds of which synthetic methods are not mentioned in the presentdisclosure are all raw material products obtained by commercial routes.

The synthetic methods of the organic compounds of the present disclosureare specifically described below in conjunction with synthesis examples.

SYNTHESIS EXAMPLES

1. Preparation of Intermediate IM a-1

2-Bromo-4-chloro-1-iodobenzene (50.0 g, 157.5 mmol),dibenzofuran-3-boronic acid (30.4 g, 157.5 mmol),tetrakis(triphenylphosphine)palladium (3.6 g, 3.1 mmol), potassiumcarbonate (54.3 g, 393.8 mmol), and tetrabutylammonium bromide (10.1 g,31.5 mmol) were added to a flask, and a mixed solvent of toluene (440mL), ethanol (200 mL) and water (100 mL) was added, and the mixture washeated to 80° C. under nitrogen protection, and stirred for 24 h whilemaintaining the temperature, after cooling to room temperature, stirringwas stopped, the reaction solution was washed with water, the obtainedorganic phase was separated, and dried by anhydrous magnesium sulfate,and a solvent was removed under reduced pressure to give a crudeproduct; and the crude product was purified by silica gel columnchromatography using dichloromethane/n-heptane as a mobile phase toobtain a white solid intermediate IM a-1 (33.8 g, yield: 60%).

Intermediates IM x-1 listed in Table 1 were synthesized by the samemethod as that for synthesis of the intermediate IM a-1 except that areactant A was used instead of 2-bromo-4-chloro-l-iodobenzene and areactant B was used instead of dibenzofuran-3-boronic acid. The usedmain reactants, the synthesized intermediates and their yields are shownin Table 1.

TABLE 1 Yield/ Reactant A Reactant B Intermediate IM x-1 %

60

58

61

63

57

59

60

64

56

67

62

64

66

63

62

61

60

59

64

65

63

58

58

59

61

2. Preparation of Intermediate IM a-2

The intermediate IM a-1 (33.8 g, 94.5 mmol) and tetrahydrofuran (280 mL)were added to a flask, and cooled to −78° C. under nitrogen protection,a solution (2.5 M) of n-butyllithium (57 mL, 141.75 mmol) intetrahydrofuran was added dropwise under stirring, after the dropwiseaddition was complete, stirring was performed for 1 h while heatpreservation, a solution of adamantanone (11.3 g, 75.6 mmol) intetrahydrofuran (56 mL) was added dropwise while maintaining at −78° C.,after the addition was complete, heat preservation was performed for 1h, then the system was heated to room temperature, stirring wasperformed for 24 h, hydrochloric acid (12M) (17.7 mL, 212.59 mmol) (100mL) was added to the reaction solution, stirring was performed for 1 h,liquid separation was performed, the obtained organic phase was washedwith water to be neutral, and dried by anhydrous magnesium sulfate, anda solvent was removed under reduced pressure to obtain a crude product,and the crude product was purified by silica gel column chromatographyusing a dichloromethane/n-heptane system to obtain a white solidintermediate IM a-2 (20.3 g, yield: 50%).

Intermediates IM x-2 listed in Table 2 were synthesized by the samemethod as that for synthesis of the intermediate IM a-2 except that areactant C was used instead of the intermediate IM a-1. The used mainreactants, the synthesized intermediates and their yields are shown inTable 2.

TABLE 2 Reactant C Intermediate IM x-2 Yield/%

56

54

53

52

51

57

50

59

57

55

54

52

54

56

53

52

53

59

58

60

63

59

61

59

58

3. Preparation of Intermediate IM a-3

The intermediate IM a-2 (20.3 g, 47.3 mmol) and glacial acetic acid (200mL) were added into a flask, a solution of concentrated sulfuric acid(98%) (0.9 mL, 9.5 mmol) in acetic acid (20 mL) was slowly addeddropwise under stirring at room temperature under nitrogen protection,and after the dropwise addition was complete, the mixture was heated to60° C., and stirred for 2 h; the resulting reaction solution was cooledto room temperature, the precipitated solid was filtered, and a filtercake was rinsed with water and ethanol, and oven-dried to obtain a crudeproduct; and the crude product was purified by silica gel columnchromatography using a dichloromethane/n-heptane system to obtain awhite solid intermediate IM a-3 (15.5 g, yield: 80%).

Intermediates IM x-3 listed in Table 3 were synthesized by the samemethod as that for synthesis of the intermediate IM a-3 except that thereactant D was used instead of the intermediate IM a-2. The used mainreactants, the synthesized intermediates and their yields are shown inTable 3.

TABLE 3 Reactant D Intermediate x-3 Yield/%

76

77

73

72

79

80

75

73

75

72

69

68

79

76

73

71

70

79

80

81

77

78

74

73

72

4. Preparation of Intermediate IM a-4

The intermediate IM a-3 (15.5 g, 37.7 mmol), bis(pinacolato)diboron(11.5 g, 45.3 mmol), tris(dibenzylideneacetone)dipalladium (0.35 g, 0.38mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.35 g,0.75 mmol), potassium acetate (11.1 g, 113.1 mmol) and 1,4-dioxane (150mL) were added to a flask, and stirred under reflux at 100° C. for 12 hunder nitrogen protection; the resulting reaction solution was cooled toroom temperature, dichloromethane and water were added to the reactionsolution, liquid separation was performed, the obtained organic phasewas washed with water and dried by anhydrous magnesium sulfate, and asolvent was removed under reduced pressure to obtain a crude product;and the crude product was purified by silica gel column chromatographyusing a dichloromethane/n-heptane system to obtain a white solidintermediate IM a-4 (10.0 g, yield: 53%).

Intermediates IM x-4 listed in Table 4 were synthesized by the samemethod as that for synthesis of the intermediate IM a-4 except that areactant E was used instead of the intermediate IM a-3. The used mainreactants, the synthesized intermediates and their yields are shown inTable 4.

TABLE 4 Reactant E Intermediate IM x-4 Yield/%

53

52

50

56

57

58

55

59

58

58

56

54

60

59

56

55

57

58

57

55

54

57

52

59

58

5. Preparation of Compounds

The intermediate TM a-4 (10 g, 19.9 mmol),2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-triazine (6.2 g, 18.1 mmol),tetrakis(triphenylphosphine)palladium (0.41 g, 0.36 mmol), potassiumcarbonate (6.2 g, 45.2 mmol), and tetrabutylammonium bromide (1.1 g, 3.6mmol) were added to a flask, and a mixed solvent of toluene (80 mL),ethanol (20 mL) and water (20 mL) was added, and the mixture was heatedto 80° C. under nitrogen protection, and stirred for 8 h whilemaintaining the temperature; then cooling to room temperature, stirringwas stopped, the reaction solution was washed with water, the obtainedorganic phase was separated, and dried by anhydrous magnesium sulfate,and a solvent was removed under reduced pressure to obtain a crudeproduct; and the crude product was purified by silica gel columnchromatography using a dichloromethane/n-heptane mixed solvent as amobile phase to obtain a white solid compound 2 (8.6 g, yield: 70%).

Compounds listed in Table 5 were synthesized by the same synthesismethod as that for the synthesis of the compound 2 except that areactant F was used instead of the intermediate IM a-4, and a reactant Gwas used instead of 2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-triazine. Theused main reactants, the synthesized compounds and their yields areshown in Table 5.

TABLE 5 Yield/ Reactant F Reactant G Compound %

69

60

63

60

68

64

71

72

59

60

67

54

68

59

68

68

62

56

66

55

70

64

57

63

66

68

66

64

Preparation of Compound 374:

(1) Synthesis of Intermediate IM A

8-Bromonaphtho[1,2-B]benzofuran (50 g, 168.2 mmol) and tetrahydrofuran(400 ml) were added to a flask, and cooled to −78° C. under nitrogenprotection, a solution (2.5 M) of n-butyllithium (72.4 mL, 181.1 mmol)in tetrahydrofuran was added dropwise under stirring, after the dropwiseaddition was complete, stirring was performed for 1 h while heatpreservation, a solution of trimethyl borate (17.5 g, 168.2 mmol) intetrahydrofuran (70 mL) was added dropwise while maintaining at −78° C.,after the dropwise addition was complete, heat preservation wasperformed for 1 h, the system was heated to room temperature, stirringwas performed for 24 h, a solution of hydrochloric acid (12M) (22.6 mL,271.6 mmol) in water (113.2 mL) was added into the reaction solution,stirring was performed for 1 h, liquid separation was performed, theobtained organic phase was washed with water to be neutral, and dried byanhydrous magnesium sulfate, and a solvent was removed under reducedpressure to give a crude product, and the crude product was purified bysilica gel column chromatography using a dichloromethane/n-heptanesystem to obtain a white solid intermediate IM A (24.7 g, yield: 56%).

(2) Synthesis of Intermediate IM B

1-Bromo-2-iodonaphthalene (29.9 g, 89.8 mmol), the intermediate IM A(24.7 g, 94.2 mmol), tetrakis(triphenylphosphine)palladium (2.1 g, 1.8mmol), potassium carbonate (27.3 g, 197.5 mmol), and tetrabutylammoniumbromide (5.8 g, 17.9 mmol) was added to a flask, and a mixed solvent oftoluene (240 mL), ethanol (120 mL) and water (60 mL) was added, and themixture was heated to 80° C. under nitrogen protection, and stirred for24 h while maintaining the temperature, after cooling to roomtemperature, stirring was stopped, the reaction solution was washed withwater, the obtained organic phase was separated, and dried by anhydrousmagnesium sulfate, and a solvent removed under reduced pressure to givea crude product; and the crude product was purified by silica gel columnchromatography using dichloromethane/n-heptane as a mobile phase toobtain a white solid intermediate IM B (28.5 g, yield: 75%).

(3) Synthesis of Intermediate IM C

The intermediate IM B (28.5 g, 67.3 mmol) and tetrahydrofuran (230 mL)were added to a flask, and cooled to −78° C. under nitrogen protection,a solution (2.5 M) of n-butyllithium (32.3 mL, 80.8 mmol) intetrahydrofuran was added dropwise under stirring, after the dropwiseaddition was complete, stirring was performed for 1 h while heatpreservation, a solution of adamantanone (11.1 g, 74.0 mmol) intetrahydrofuran (44 mL) was added dropwise while maintaining at -78° C.,after the dropwise addition was complete, heat preservation wasperformed for 1 h, the system was heated to room temperature, stirringwas performed for 24 h, 50 mL of hydrochloric acid (12M) (10.1 mL, 121.2mmol) was added to the reaction solution, stirring was performed for 1h, liquid separation was performed, the obtained organic phase waswashed with water to be neutral, and dried by anhydrous magnesiumsulfate, and a solvent was removed under reduced pressure to give acrude product, and the crude product was purified by silica gel columnchromatography using a dichloromethane/n-heptane system to obtain awhite solid intermediate IM C (18.3 g, yield: 55%).

(4) Synthesis of Intermediate IM D

The intermediate IM C (18.3 g, 37.0 mmol) and glacial acetic acid (146mL) were added into a flask, and a solution of concentrated sulfuricacid (98%) (0.8 mL, 7.4 mmol) in acetic acid (15 mL) was slowly addeddropwise under stirring at room temperature under nitrogen protection,after the dropwise addition was completed, the mixture was heated to 60°C., and stirred for 2 h; the resulting reaction solution was cooled toroom temperature, the precipitated solid was filtered, and a filter cakewas rinsed with water and ethanol and oven-dried to give a crudeproduct; and the crude product was purified by silica gel columnchromatography using a dichloromethane/n-heptane system to obtain awhite solid intermediate IM D (13.6 g, yield: 77%).

(5) Synthesis of Intermediate IM E

The intermediate IM D (13.6 g, 28.5 mmol) and a solvent DMF(N,N-dimethylformamide) (110 mL) were added to a flask, and stirred atroom temperature under nitrogen protection for 10 min,N-bromosuccinimide (NBS) (7.6 g, 42.8 mmol) was added, and the mixturewas heated to 80° C., and stirred for 4 h while heat preservation; afterthe reaction was completed, the resulting reaction solution was cooledto room temperature, the reaction solution was extracted withdichloromethane and water, the obtained organic phase was taken anddried by anhydrous magnesium sulfate, and a solvent was removed underreduced pressure to give a crude product; and the crude product waspurified by silica gel column chromatography using adichloromethane/n-heptane system as a mobile phase to obtain a whitesolid intermediate IM E (11.9 g, yield: 75%).

(6) Synthesis of Intermediate IM F

The intermediate IM E (11.9 g, 21.4 mmol), bis(pinacolato)diboron (6.5g, 25.7 mmol), tris(dibenzylideneacetone)dipalladium (0.2 g, 0.2 mmol),2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.4, 0.2 mmol),potassium acetate (4.6 g, 47.1 mmol) and 1,4-dioxane (150 mL) were addedto a flask, and stirred under reflux at 100° C. for 12 h under nitrogenprotection; the resulting reaction solution was cooled to roomtemperature, dichloromethane and water were added to the reactionsolution, liquid separation was performed, the obtained organic phasewas washed with water, and dried by anhydrous magnesium sulfate, and asolvent was removed under reduced pressure to give a crude product; andthe crude product was purified by silica gel column chromatography usinga dichloromethane/n-heptane system to obtain a white solid intermediateIM F (7.74 g, yield: 60%).

(7) Synthesis of Compound 374

The intermediate IM F (7.7 g, 12.8 mmol),2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-triazine (3.3 g, 12.2 mmol),tetrakis(triphenylphosphine)palladium (0.28 g, 0.24 mmol), potassiumcarbonate (3.7 g, 26.9 mmol), and tetrabutylammonium bromide (0.8 g, 2.4mmol) were added to a flask, and a mixed solvent of toluene (60 mL),ethanol (30 mL) and water (15 mL) was added, and the mixture was heatedto 80° C. under nitrogen protection, and stirred for 8 h whilemaintaining the temperature; then cooling to room temperature, stirringwas stopped, the reaction solution was washed with water, the obtainedorganic phase was separated, and dried by anhydrous magnesium sulfate,and a solvent was removed under reduced pressure to obtain a crudeproduct; and the crude product was purified by silica gel columnchromatography using a dichloromethane/n-heptane mixed solvent as amobile phase to obtain a white solid compound 374 (5.6 g, yield: 65%).

The above synthesized compounds were subjected to mass spectrometry andthe results are shown in Table 6:

TABLE 6 Mass spectrometric data for compounds Compound 2  m/z = 684.3Compound 98  m/z = 800.2 Compound 4  m/z = 608.3 [M + H]⁺ [M + H]⁺ [M +H]⁺ Compound 7  m/z = 698.3 Compound 116 m/z = 713.3 Compound 125 m/z =710.3 [M + H]⁺ [M + H]⁺ [M + H]⁺ Compound 13 m/z = 636.3 Compound 135m/z = 724.3 Compound 144 m/z = 750.4 [M + H]⁺ [M + H]⁺ [M + H]⁺ Compound23 m/z = 605.3 Compound 28  m/z = 734.3 Compound 154 m/z = 595.3 [M +H]⁺ [M + H]⁺ [M + H]⁺ Compound 44 m/z = 734.3 Compound 159 m/z = 786.4Compound 167 m/z = 709.4 [M + H]⁺ [M + H]⁺ [M + H]⁺ Compound 48 m/z =684.3 Compound 58  m/z = 728.3 Compound 209 m/z = 756.3 [M + H]⁺ [M +H]⁺ [M + H]⁺ Compound 59 m/z = 730.2 Compound 237 m/z = 652.3 Compound60  m/z = 804.3 [M + H]⁺ [M + H]⁺ [M + H]⁺ Compound 64 m/z = 623.2Compound 322 m/z = 569.3 Compound 261 m/z = 658.3 [M + H]⁺ [M + H]⁺ [M +H]⁺ Compound 67 m/z = 597.2 Compound 323 m/z = 585.3 Compound 90  m/z =724.3 [M + H]⁺ [M + H]⁺ [M + H]⁺ Compound 78 m/z = 700.3 Compound 324m/z = 579.3 Compound 374 m/z = 708.3 [M + H]⁺ [M + H]⁺ [M + H]⁺

NMR data for compounds are as follows:

Compound 2:

¹H-NMR (CD₂Cl₂, 400 MHz): 8.81 (d, 2H), 8.20-8.17 (m, 3H), 8.04-7.97 (m,3H), 7.86 (d, 2H), 7.66-7.56 (m, 4H), 7.54-7.39 (m, 8H), 7.31 (t, 1H),2.83 (d, 2H), 2.71 (d, 2H), 2.14 (s, 1H), 2.06 (s, 1H), 1.89 (s, 2H),1.73 (t, 4H), 1.46 (s, 2H).

Compound 23:

¹H-NMIR (CD₂Cl₂, 400 MHz): 8.14 (d, 2H), 8.08-8.06 (m, 2H), 7.86 (t,2H), 7.78 (d, 1H), 7.70 (s, 1H), 7.63 (d, 4H), 7.52 (t, 4H), 7.47-7.33(m, 5H), 7.27 (t, 1H), 2.80 (d, 2H), 2.73 (d, 2H), 2.14 (s, 1H), 2.07(s, 1H), 1.88 (s, 2H), 1.72 (t, 4H), 1.38 (s, 2H).

Compound 78:

¹H-NMR (CD₂Cl₂, 400 MHz): 8.79 (d, 2H), 8.34 (s, 1H), 8.29 (d, 1H),8.20-8.16 (m, 3H), 8.07 (s, 1H), 8.01 (d, 2H), 7.86 (d, 2H), 7.75 (d,1H), 7.66-7.51 (m, 8H), 7.43-7.38 (m, 1H), 7.30-7.26 (m, 1H), 2.84 (d,2H), 2.75 (d, 2H), 2.12 (s, 1H), 2.06 (s, 1H), 1.86 (s, 2H), 1.70 (t,4H), 1.36 (s, 2H).

Example 1: Green Organic Electroluminescent Device

A green organic electroluminescent device was manufactured by using thefollowing method:

an anode was prepared by the following process: an ITO substrate with anITO thickness of 1500 Å was cut into a dimension of 40 mm (length)×40 mm(width)×0.7 mm (thickness) to be prepared into an experimental substratewith a cathode, an anode and an insulating layer pattern by adopting aphotoetching process, and surface treatment was performed by ultravioletozone and O₂:N₂ plasma to increase the work function of the anode, andthe surface of the ITO substrate may be cleaned with an organic solventto clean impurities and gungo on the surface of the ITO substrate.

F4-TCNQ was vacuum evaporated on the experimental substrate (the anode)to form a hole injection layer (HIL) having a thickness of 100 Å, andHT-01 was evaporated on the hole injection layer to form a first holetransport layer with a thickness of 850 Å.

HT-02 was vacuum evaporated on the first hole transport layer to form asecond hole transport layer with a thickness of 350 Å.

A compound 23, GHn1 and Ir(ppy)3 were co-evaporated at a ratio of50%:45%:5% (an evaporation rate) on the second hole transport layer toform a green light-emitting layer (EML) with a thickness of 400 Å.

ET-01 and LiQ were mixed at a weight ratio of 1:1 and evaporated to forman electron transport layer (ETL) having a thickness of 300 Å, LiQ wasevaporated on the electron transport layer to form an electron injectionlayer (EIL) having a thickness of 10 Å, and then magnesium (Mg) andsilver (Ag) were mixed and vacuum evaporated at an evaporation rate of1:9 on the electron injection layer to form a cathode with a thicknessof 110 Å.

In addition, CP-01 with a thickness of 650 Å was evaporated on thecathode to form an organic capping layer (CPL), thus completing themanufacture of the entire organic light-emitting device.

Examples 2-10

The organic electroluminescent devices were manufactured by the samemethodas as that in Example 1, except that a mixed component shown inTable 7 below was used instead of the mixed component in Example 1 whenthe organic light-emitting layer was formed.

Comparative Examples 1-3

The organic electroluminescent devices were manufactured by the samemethodas as that in Example 1, except that a mixed component shown inTable 7 below was used instead of the mixed component in Example 1 whenthe organic light-emitting layer was formed.

The structures of main materials used in Examples 1-10 and Comparativeexamples 1-3 are shown below:

The organic electroluminescent devices manufactured in Examples 1-10 andComparative examples 1-3 were subjected to performance tests under acondition of 20 mA/cm², and the test results are shown in Table 7 below.

TABLE 7 Performance test results of organic electroluminescent deviceExternal Light-emitting quantum T95 layer Driving Current PowerChromaticity efficiency service three materials = voltage efficiencyefficiency coordinate EQE life Example No. 50%:45%:5% (V) (Cd/A) (lm/W)CIEx, CIEy (%) (h) Example 1 Compound 3.78 80.5 66.9 0.22, 0.73 18.2 21623:GHn1:Ir(ppy)₃ Example 2 Compound 3.76 82.3 68.7 0.22, 0.73 18.8 219323:GHn1:Ir(ppy)₃ Example 3 Compound 3.80 82.8 68.4 0.22, 0.73 19.2 221324:GHn1:Ir(ppy)₃ Example 4 GHp1:Compound 3.77 83.2 69.3 0.22, 0.73 19.3227 64:Ir(ppy)₃ Example 5 GHp1:Compound 3.70 84.5 71.7 0.22, 0.73 18.2226 67:Ir(ppy)₃ Example 6 GHp1:Compound 3.70 87.3 74.1 0.22, 0.73 18.4232 2:Ir(ppy)₃ Example 7 GHp1:Compound 3.69 86.8 73.9 0.22, 0.73 19.1236 4:Ir(ppy)₃ Example 8 GHp1:Compound 3.66 89.8 77.0 0.22, 0.73 19.4240 7:Ir(ppy)₃ Example 9 GHp1:Compound 3.62 88.3 76.6 0.22, 0.73 18.8237 13:Ir(ppy)₃ Example 10 GHp1:Compound 3.70 89.1 75.6 0.22, 0.73 18.6241 28:Ir(ppy)₃ Comparative Compound 3.71 68.2 57.7 0.22, 0.73 16.4 154example 1 A:GHn1:Ir(ppy)₃ Comparative Compound 3.80 73.2 60.5 0.22, 0.7317.6 152 example 2 B:GHn1:Ir(ppy)₃ Comparative GHp1:Compound 3.69 66.956.9 0.22, 0.73 16.4 176 example 3 C:Ir(ppy)₃

From the data shown in Table 7, it can be seen that the organicelectroluminescent devices manufactured in Examples 1-10 have theadvantages that the driving voltages were substantially similar, theluminous efficiency was improved by at least 10%, and the service lifeof the devices were prolonged by at least 23% compared with the organicelectroluminescent devices manufactured in Comparative examples 1-3. Itcan be seen that when the organic compound of the present disclosure isused as an organic light-emitting layer material of the organicelectroluminescent device, in particular a host material, the efficiencyperformance and the service life of the organic electroluminescentdevice can be effectively improved.

Example 11: Red Organic Electroluminescent Device

An anode was prepared by the following process: an ITO substrate with anITO thickness of 1500 Å was cut into a dimension of 40 mm (length)×40 mm(width)×0.7 mm (thickness) to be prepared into an experimental substratewith a cathode, an anode and an insulating layer pattern by adopting aphotoetching process, and surface treatment was performed by ultravioletozone and O₂:N₂ plasma to increase the work function of the anode, andthe surface of the ITO substrate may be cleaned with an organic solventto clean impurities and gungo on the surface of the ITO substrate.

F4-TCNQ was vacuum evaporated on the experimental substrate (the anode)to form a hole injection layer (HIL) with a thickness of 100 Å, andHT-03 was evaporated on the hole injection layer to form a first holetransport layer with a thickness of 850 Å.

HT-04 was vacuum evaporated on the first hole transport layer to form asecond hole transport layer with a thickness of 800 Å.

A compound 44 and Ir(piq)₂(acac) were co-evaporated at a ratio of 95%:5%(an evaporation rate) on the second hole transport layer to form a redlight-emitting layer (EML) with a thickness of 350 Å.

ET-01 and LiQ were mixed at a weight ratio of 1:1 and evaporated to forman electron transport layer (ETL) having a thickness of 300 Å, LiQ wasevaporated on the electron transport layer to form an electron injectionlayer (EIL) with a thickness of 10 Å, and then magnesium (Mg) and silver(Ag) were mixed and vacuum evaporated at an evaporation rate of 1:9 onthe electron injection layer to form a cathode with a thickness of 105Å.

In addition, CP-01 with a thickness of 650 Å was evaporated on thecathode to form an organic capping layer (CPL), thus completing themanufacture of an organic light-emitting device.

Examples 12-18

The organic electroluminescent devices were manufactured by the samemethodas as that in Example 11, except that a mixed component shown inTable 8 below was used instead of the mixed component in Example 11 whenthe light-emitting layer was formed.

Comparative Examples 4-5

The organic electroluminescent devices were manufactured by the samemethodas as that in Example 11, except that a mixed component shown inTable 8 below was used instead of the mixed component in Example 11 whenthe light-emitting layer was formed.

The structures of main materials used in Examples 11-18 and Comparativeexamples 4-5 are shown below:

The organic electroluminescent devices manufactured in Examples 11-18and Comparative examples 4-5 were subjected to performance tests under acondition of 20 mA/cm², and the test results are shown in Table 8 below.

TABLE 8 Performance test results of organic electroluminescent deviceExternal quantum T95 Driving Current Power Chromaticity efficiencyservice Compound:Ir(piq)₂ voltage efficiency efficiency coordinate EQElife Example No. (acac) = 95%:5% (V) (Cd/A) (lm/W) CIEx, CIEy (%) (h)Example 11 Compound 44 3.78 39.0 32.4 0.68, 0.32 27.4 430 Example 12Compound 48 3.74 39.2 32.9 0.68, 0.32 27.3 428 Example 13 Compound 583.73 41.5 34.9 0.68, 0.32 28.4 401 Example 14 Compound 59 3.76 38.6 32.20.68, 0.32 26.0 458 Example 15 Compound 60 3.71 41.6 35.2 0.68, 0.3227.9 387 Example 16 Compound 78 3.70 40.8 34.6 0.68, 0.32 27.6 412Example 17 Compound 90 3.72 38.9 32.8 0.68, 0.32 26.5 452 Example 18Compound 374 3.73 39.4 33.2 0.68, 0.32 26.8 445 Comparative Compound D4.05 27.7 21.4 0.68, 0.32 20.2 270 example 4 Comparative Compound E 3.7828.5 23.6 0.68, 0.32 19.4 270 example 5

From the data shown in Table 8, it can be seen that the organicelectroluminescent devices manufactured in Examples 11-18 have theadvantages that the driving voltages are similar, the luminousefficiency of the devices were improved by at least 35%, and the servicelife was prolonged by at least 43% compared with the organicelectroluminescent devices manufactured in Comparative example 5. Theorganic electroluminescent devices manufactured in Examples 11-18 havethe advantages that the driving voltage was reduced by at least 7%, theluminous efficiency was improved by at least 39%, and the service lifewas prolonged by at least 43% compared with Comparative example 4. Itcan be seen that when the compounds of the present disclosure are usedas an organic light-emitting layer material of the organicelectroluminescent device, in particular a host material, the efficiencyperformance and the service life performance of the organicelectroluminescent device can be improved.

In the compounds of the present disclosure, spiro[adamantane-fusedfluorenyl] as a part of a core is a large planar conjugated structure,which has a strong rigidity and thus the compounds of the presentdisclosure have a high first triplet energy level, conjugated connectionwith a fused heteroaromatic ring in the compounds has a better holetransport ability, adamantyl is spiro-bonded to fluorenyl, so that theelectron cloud density of the large planar conjugate structure can begreatly increased by a hyperconjugation effect, enhancing the holemobility of the compounds, helping to promote the transport balance ofholes and electrons in the light-emitting layer, and improving theefficiency performance of the organic electroluminescent device, andthus the compounds of the present disclosure are suitable as the hostmaterial of the organic light-emitting layer in the organicelectroluminescent device. Not only that, the improvement of the holetransport performance of the compounds can improve the recombinationrate of electrons and holes in the organic light-emitting layer, andreduce or avoid the transport of electrons to the hole transport layerthrough the organic light-emitting layer, and then, the hole transportlayer material may be effectively protected from the impact ofelectrons, improving the service life of the organic electroluminescentdevice. Moreover, adamantyl spiro-bonded to fluorenyl has a large spacevolume and strong rigidity, thus, it is possible to reduce theinteraction force between large planar conjugated structures, reduceintermolecular π-π stacking, and adjust the degree of intermolecularstacking, thus enabling the compounds to have a more stable amorphousform during film formation, and improving the film-forming properties ofthe compounds, and thus further improving the service life of theorganic electroluminescent device.

Preferred examples of the present disclosure have been described indetail above, but the present disclosure is not limited to specificdetails in the above-described examples, and many simple modificationsmay be made to the technical solutions of the present disclosure withinthe technical idea of the present disclosure, and these simplemodifications are all within the scope of protection of the presentdisclosure. In addition, it should be noted that various specifictechnical features described in the above specific examples may becombined in any suitable manner without contradiction. In order to avoidunnecessary repetition, the present disclosure does not further describethe various possible combinations.

1. An organic compound, having a structure consisting of a structurerepresented by a formula I and a structure represented by a formula II:

wherein the structure represented by the formula I is fused with atleast one structure represented by the formula II; * represents a sitewhere the formula I is fused with the formula II; a ring A is selectedfrom a benzene ring or a fused aromatic ring with 10 to 14 ring-formingcarbon atoms; n₁ represents the number of R₁, n₂ represents the numberof R₂, and n₃ represents the number of R₃; R₁, R₂ and R₃ are representedby R_(k), n₁ to n₃ are represented by n_(k), and k is a variable andrepresents 1, 2 or 3; in response to determining that k is 1, n_(k) isselected from 0, 1, 2, 3 or 4; in response to determining that k is 2,n_(k) is selected from 0, 1 or 2; in response to determining that k is3, n_(k) is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; and in responseto determining that n_(k) is greater than 1, any two n_(k) are the sameor different; and optionally, any two adjacent R_(k) are connected toeach other to form a ring, and the formed ring is optionally substitutedwith R′; R₁, R₂, R₃, and R′ are the same or different, and are eachindependently selected from an alkyl with 1 to 5 carbon atoms or astructure represented by a formula III:—(L)_(m)—Ar m represents the number of L, and m is selected from 0, 1, 2or 3; and in response to determining that m is 2 or 3, any two L are thesame or different; Ar is selected from a substituted or unsubstitutedaryl with 6 to 30 carbon atoms, a substituted or unsubstitutedheteroaryl with 3 to 30 carbon atoms; L is selected from a single bond,a substituted or unsubstituted arylene with 6 to 30 carbon atoms, or asubstituted or unsubstituted heteroarylene with 3 to 30 carbon atoms;substituents in L and Ar are one or more, wherein the substituents in Land Ar are each independently selected from deuterium, a halogen group,cyano, a heteroaryl with 3 to 12 carbon atoms, an aryl with 6 to 12carbon atoms, an alkyl with 1 to 5 carbon atoms, or trimethylsilyl; andX and Y are the same or different, and are each independently selectedfrom a single bond, O, S, C(R₄R₅), and Si(R₆R₇), and X and Y are notsimultaneously a single bond; wherein R₄ to R₇ are the same ordifferent, and are each independently selected from an alkyl with 1 to 5carbon atoms, an unsubstituted aryl with 6 to 20 carbon atoms, or anunsubstituted heteroaryl with 3 to 20 carbon atoms; optionally, R₄ andR₅ are connected to each other to form a 3- to 15-membered saturated orunsaturated ring together with the atoms to which they are commonlyconnected; and optionally, R₆ and R₇ are connected to each other to forma 3- to 15-membered saturated or unsaturated ring together with theatoms to which they are commonly connected.
 2. The organic compoundaccording to claim 1, wherein the organic compound has a structure shownin any one of formulae 1-1 to 1-17:

wherein n′₁ is selected from 0, 1 or 2; and n′₂ is selected from 0, 1 or2.
 3. The organic compound according to claim 1, wherein the organiccompound has a structure shown in any one of 2-1 to 2-41:

wherein n′₂ is selected from 0, 1 or
 2. 4. The organic compoundaccording to claim 1, wherein the formula II has a structure shown inany one of formulae II-1 to II-11:


5. The organic compound according to claim 1, wherein the ring A isselected from a benzene ring, a naphthalene ring, an anthracene ring, ora phenanthrene ring.
 6. (canceled)
 7. The organic compound according toclaim 1, wherein L is selected from a single bond, a substituted orunsubstituted arylene with 6 to 15 carbon atoms, or a substituted orunsubstituted heteroarylene with 3 to 20 carbon atoms.
 8. The organiccompound according to claim 1, wherein L is selected from a single bondor a substituted or unsubstituted group T₁, wherein the unsubstitutedgroup T₁ is selected from the group consisting of:

the substituted group T₁ has one or two or more substituents, and thesubstituents in substituted group T₁ are independently selected fromdeuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, methyl,ethyl, isopropyl, tent-butyl, phenyl, biphenyl, pyridyl, naphthyl,carbazolyl, dibenzofuranyl or dibenzothienyl.
 9. The organic compoundaccording to claim 1, wherein L is selected from a single bond or thegroup consisting of:


10. (canceled)
 11. The organic compound according to claim 1, wherein Aris selected from a substituted or unsubstituted aryl with 6 to 25 carbonatoms or a substituted or unsubstituted heteroaryl with 3 to 20 carbonatoms.
 12. The organic compound according to claim 1, wherein Ar isselected from a substituted or unsubstituted group T₂, wherein theunsubstituted group T₂ is selected from the group consisting of:

the substituted group T₂ has one or two or more sub stituents, and thesub stituents in the substituted group T₂ are independently selectedfrom deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl,phenyl, biphenyl, pyridyl, naphthyl, carbazolyl, cyclohexyl,dibenzofuranyl or dibenzothienyl.
 13. The organic compound according toclaim 1, wherein Ar is selected from the following groups:


14. (canceled)
 15. (canceled)
 16. The organic compound according toclaim 1, wherein the organic compound is selected from the groupconsisting of the following compounds:


17. An electronic element, comprising an anode and a cathode which areoppositely disposed, and a functional layer disposed between the anodeand the cathode; and the functional layer comprises the organic compoundaccording to claim
 1. 18. The electronic element according to claim 17,wherein the functional layer comprises an organic light-emitting layer,and the organic light-emitting layer comprises the organic compound. 19.The electronic element according to claim 17, wherein the electronicelement is an organic electroluminescent device.
 20. An electronicdevice, comprising the electronic element according to claim
 17. 21. Theelectronic element according to claim 19, wherein the organicelectroluminescent device is a green device or a red device